Sialic carbohydrates

Abstract

The invention relates to the use of sialic carbohydrates of general formula (I), containing at least one carbohydrate unit of general formula (II) for the immune modulation, immune suppression and in the prevention and treatment of infections in humans and animals. In said formula (II), Sia represents a sialic acid or a sialic acid derivative in an α2-3 bond, Gal represents a galactose-monosaccharide-unit, HexNac represents an N-acetylated galactosamine or glucosamine-monosaccharide-unit (GalNAc or GlcNAc), Hex represents a galactose- or glucose-monosaccharide-unit (Gal or Glc), C represents HexNac or Hex or is absent, n represents 1-50, V represents OH, a carbohydrate radical or a connecting point on a support T, with the proviso that if V represents OH, n represents 1, and if V represents a carbohydrate radical or a support T, n represents the number of carbohydrate unites of general formula (II) directly connected to said carbohydrate radical or support, X represents a sialic acid or a sialic acid derivative, wherein a second sialic acid or a sialic acid derivative or more sialic acid or sialic acid derivatives can be connected to an α2-8 bond, a phosphate, a sulphate, or carboxyl-group or a monosaccharide having a phosphate, sulphate, or carboxyl group and only one of the radicals X is present.

1 . Use of sialyzed carbohydrates of the following general formula I having at least one carbohydrate unit of the following general formula II:  
       
         
           
           
               
               
           
         
       
       wherein 
 Sia means a sialic acid or a sialic acid derivative in an α2-3 bond,  
 Gal means a galactose-monosaccharide unit,  
 HexNac means an N-acetylated galactosamine-monosaccharide unit or glucosamine-monosaccharide unit (GalNAc or GlcNAc),  
 Hex means a galactose-monosaccharide unit or glucose-monosaccharide unit (Gal or Glc),  
 C represents HexNac or Hex or is absent,  
 n represents 1 to 50,  
 V represents OH, a carbohydrate residue or a connecting point on a carrier T, with the proviso that, if V represents OH, n represents 1, and, if V represents a carbohydrate residue or a carrier T, n means the number of the carbohydrate units that are each directly bound to this carbohydrate residue or carrier and which are of the general formula II  
                     
 X means a sialic acid or a sialic acid derivative thereof, wherein a second sialic acid or a sialic acid derivative or several sialic acids or sialic acid derivatives can be bound to the sialic acid or the sialic acid derivative in an α2-8 bond, a phosphate group, sulphate group or carboxyl group, or a monosaccharide including a phosphate group, sulphate group or carboxyl group, and only one of the residues X is present,  
 for the immunomodulation, immunosuppression and prevention as well as treatment of infections in humans and animals.  
 
     
     
         2 . Use according to  claim 1 , characterized in that one, two, three, four, or all of the following criteria i) through iv) are met: 
 i) Sia represents acetyl neuraminic acid (NeuAc) or N-glycolyl neuraminic acid (NeuGc),    ii) the sialic acid derivative or the sialic acid derivatives of the residues Sia and X is/are an O-acyl derivative and in particular an O-acetyl derivative,    iii) the carrier T is a peptide, a protein, a polymer or a biopolymer, with the linkage with said peptide or protein in particular being N-glycosidic or O-glycosidic, and    iv) the carbohydrate residue constituting the residue V is a monosaccharide residue, an oligosaccharide residue or a polysaccharide residue.    
     
     
         3 . Use according to  claim 1 , characterized in that the carbohydrates of general formula I are selected from disialyl-lacto-N-tetraose (DS-LNT, V=OH, HexNac=GlcNAc, Hex=galactose (Gal), C=glucose, Sia=α2-3 NeuAc, X=α2-6 NeuAc on HexNac), disialyl-lacto-N-neo-tetraose (DS-LNnT), glycomacropeptide (GMP), ganglioside G D1a , ganglioside G T1b  and ganglioside G T1c .  
     
     
         4 . Use according to  claim 1  any one of claims  1 , characterized in that T represents lipophilic compounds, and the carbohydrate unit or carbohydrate units of general formula II represents or represent the head group(s) thereof.  
     
     
         5 . Use according to  claim 4 , characterized in that said lipophilic compounds are glycolipids and in particular gangliosides.  
     
     
         6 . Use according to  claim 1 , characterized in that the carbohydrate or carbohydrates of general formula I is/are used in an amount of at least 1 mg per kg of body weight.  
     
     
         7 . Use according to  claim 1 , for the prevention and treatment of infections of the gastrointestinal tract, blood system, respiratory passages, urogenital tract, as well as the nasopharynx.  
     
     
         8 . Use according to  claim 1 , characterized in that the carbohydrate or carbohydrates of general formula I are incorporated into a fluid or solid food composition (with the exception of human milk), dietetic composition or pharmaceutical composition for administration to a human or an animal, or serve for the preparation of such a composition for the immunomodulation, immunosuppression and treatment of infections in humans and animals.  
     
     
         9 . Use according to  claim 8 , characterized in that the pharmaceutical composition serves for an oral, lingual, nasal, bronchial, vaginal, topical (skin and mucosa) and per os administration, for an administration by means of a probe into the stomach of a human or an animal, or for an administration as an infusion.  
     
     
         10 . Food composition, dietetic composition or pharmaceutical composition containing at least one carbohydrate of general formula I as described in  claim 1 .  
     
     
         11 . Composition according to  claim 10 , characterized in that the composition may contain a further carbohydrate or several further carbohydrates, which are different from the carbohydrates of  claim 1 , a further active agent or several further active agents and/or a further ingredient, which is known and suited for the corresponding composition, or more of such ingredients, wherein in the case of a pharmaceutical composition a usual auxiliary agent or several usual auxiliary agents, including diluents, moisturizing agents, thickening agents, flavoring agents, sweetening agents and carriers, may be present, and in the case of a food composition or a dietetic composition, at least one further food component may be present.  
     
     
         12 . Method of immunomodulation, immunosuppression and treatment of infections in humans and animals, characterized in that at least one carbohydrate of general formula I or a composition according to  claim 10  is administered to a human or an animal, but not in the form of human milk, in particular in such an amount that at least 1 mg of carbohydrate of general formula I is administered per kg of body weight to the human or the animal once daily.  
     
     
         13 . Sialyzed carbohydrates of the following general formula I having at least one carbohydrate unit of the following general formula II:  
       
         
           
           
               
               
           
         
       
       wherein 
 Sia means a sialic acid or a sialic acid derivative in an α2-3 bond,  
 Gal means a galactose-monosaccharide unit,  
 HexNac means an N-acetylated galactosamine-monosaccharide unit or glucosamine-monosaccharide unit (GalNAc or GlcNAc),  
 Hex means a galactose-monosaccharide unit or glucose-monosaccharide unit (Gal or Glc),  
 C represents HexNac or Hex or is absent,  
 n represents 1 to 50,  
 V represents OH, a carbohydrate residue or a connecting point on a carrier T, with the proviso that, if V represents OH, n represents 1, and, if V represents a carbohydrate residue or a carrier T, n means the number of the carbohydrate units that are each directly bound to this carbohydrate residue or carrier and which are of the general formula II  
                     
 X means a sialic acid or a sialic acid derivative thereof, wherein a second sialic acid or a sialic acid derivative or several sialic acids or sialic acid derivatives can be bound to the sialic acid or the sialic acid derivative in an α2-8 bond, a phosphate group, sulphate group or carboxyl group, or a monosaccharide including a phosphate group, sulphate group or carboxyl group, and only one of the residues X is present,  
 for the immunomodulation, immunosuppression and prevention as well as treatment of infections in humans and animals.